Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Authors

Anne T. Hylden, College of Saint Benedict/Saint John's University
Eric J. Uzelac, College of Saint Benedict/Saint John's University
Zeljko Ostojic, College of Saint Benedict/Saint John's University
Ting-Ting Wu, College of Saint Benedict/Saint John's University
Keely L. Sacry, College of Saint Benedict/Saint John's University
Krista L. Sacry, College of Saint Benedict/Saint John's University
Lin Xi, College of Saint Benedict/Saint John's University
T. Nicholas Jones, College of Saint Benedict/Saint John's UniversityFollow

Document Type

Article

Publication Date

2011

Disciplines

Chemistry | Organic Chemistry | Physical Sciences and Mathematics

Abstract

The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.

Comments

DOI: 10.3762/bjoc.7.155

Recommended Citation

Hylden, A. T.; Uzelac, E. J.; Ostojic, Z.; Wu, T-T; Sacry, K. L.; Sacry, K. L.; Xi, L.; Jones, T. N.* Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones. Beilstein J. Org. Chem., 2011, 7, 1323-1326.